A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control

Direct enantiocontrolled access to 1,3‐amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama‐aldol addition). The obtained δ‐hydroxyesters were redu...

Full description

Saved in:
Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-09, Vol.2007 (26), p.4293-4297
Main Authors: Broustal, Garance, Ariza, Xavier, Campagne, Jean-Marc, Garcia, Jordi, Georges, Yohan, Marinetti, Angela, Robiette, Raphaël
Format: Article
Language:English
Subjects:
1,5‐Diols
5-Diols
Aldol reactions
Allylation
Carbamates
Chemical Sciences
Organic chemistry
Palladium
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c3613-a3d6ed49112f92fdb1ab46658b7a2881ccfa3bfbd412a0a0d48e73cd6b9ba6d33
cites cdi_FETCH-LOGICAL-c3613-a3d6ed49112f92fdb1ab46658b7a2881ccfa3bfbd412a0a0d48e73cd6b9ba6d33
container_end_page 4297
container_issue 26
container_start_page 4293
container_title European Journal of Organic Chemistry
container_volume 2007
creator Broustal, Garance
Ariza, Xavier
Campagne, Jean-Marc
Garcia, Jordi
Georges, Yohan
Marinetti, Angela
Robiette, Raphaël
description Direct enantiocontrolled access to 1,3‐amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama‐aldol addition). The obtained δ‐hydroxyesters were reduced to pent‐2‐ene‐1,5‐diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3‐asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six‐membered‐ring cyclic carbamates. Calculations enabled us to rationalize the observed stereoselectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
doi_str_mv 10.1002/ejoc.200700503
format article
fullrecord <record><control><sourceid>wiley_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00175948v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>EJOC200700503</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3613-a3d6ed49112f92fdb1ab46658b7a2881ccfa3bfbd412a0a0d48e73cd6b9ba6d33</originalsourceid><addsrcrecordid>eNqFkM9LwzAYhoso-PPqOVfBzi9NljbeStFNHU50orfwNUlZtV1GUqb77-2YDG-evpeX5_kObxSdUxhQgOTKfjg9SABSgCGwveiIgpQxCAn7feaMx1Sy98PoOIQPAJBC0KPI5-Sls966YBuru3plSb5ceod6TjpH6CWL87ZeOJI32s1dE8iTd11PWkMwkGKtm1qTAn2JLXY2XJOHemG7vluFAZnNrW-dWS-w3VBu0XnXnEYHFTbBnv3ek-j19mZWjOPJdHRX5JNYM0FZjMwIa7ikNKlkUpmSYsmFGGZlikmWUa0rZGVVGk4TBATDM5sybUQpSxSGsZPoYvt3jo1a-rpFv1YOazXOJ2rTAdB0KHm2oj072LLauxC8rXYCBbVZV23WVbt1e0Fuha-6set_aHVzPy3-uvHWrUNnv3cu-k8lUpYO1dvjSPHnCafjt7G6Zz_IVo4y</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control</title><source>Wiley</source><creator>Broustal, Garance ; Ariza, Xavier ; Campagne, Jean-Marc ; Garcia, Jordi ; Georges, Yohan ; Marinetti, Angela ; Robiette, Raphaël</creator><creatorcontrib>Broustal, Garance ; Ariza, Xavier ; Campagne, Jean-Marc ; Garcia, Jordi ; Georges, Yohan ; Marinetti, Angela ; Robiette, Raphaël</creatorcontrib><description>Direct enantiocontrolled access to 1,3‐amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama‐aldol addition). The obtained δ‐hydroxyesters were reduced to pent‐2‐ene‐1,5‐diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3‐asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six‐membered‐ring cyclic carbamates. Calculations enabled us to rationalize the observed stereoselectivity. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2007)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200700503</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>1,5‐Diols ; 5-Diols ; Aldol reactions ; Allylation ; Carbamates ; Chemical Sciences ; Organic chemistry ; Palladium</subject><ispartof>European Journal of Organic Chemistry, 2007-09, Vol.2007 (26), p.4293-4297</ispartof><rights>Copyright © 2007 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3613-a3d6ed49112f92fdb1ab46658b7a2881ccfa3bfbd412a0a0d48e73cd6b9ba6d33</citedby><cites>FETCH-LOGICAL-c3613-a3d6ed49112f92fdb1ab46658b7a2881ccfa3bfbd412a0a0d48e73cd6b9ba6d33</cites><orcidid>0000-0002-4943-047X ; 0000-0002-4414-073X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,313,314,776,780,788,881,27901,27903,27904</link.rule.ids><backlink>$$Uhttps://hal.science/hal-00175948$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Broustal, Garance</creatorcontrib><creatorcontrib>Ariza, Xavier</creatorcontrib><creatorcontrib>Campagne, Jean-Marc</creatorcontrib><creatorcontrib>Garcia, Jordi</creatorcontrib><creatorcontrib>Georges, Yohan</creatorcontrib><creatorcontrib>Marinetti, Angela</creatorcontrib><creatorcontrib>Robiette, Raphaël</creatorcontrib><title>A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Direct enantiocontrolled access to 1,3‐amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama‐aldol addition). The obtained δ‐hydroxyesters were reduced to pent‐2‐ene‐1,5‐diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3‐asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six‐membered‐ring cyclic carbamates. Calculations enabled us to rationalize the observed stereoselectivity. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2007)</description><subject>1,5‐Diols</subject><subject>5-Diols</subject><subject>Aldol reactions</subject><subject>Allylation</subject><subject>Carbamates</subject><subject>Chemical Sciences</subject><subject>Organic chemistry</subject><subject>Palladium</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAYhoso-PPqOVfBzi9NljbeStFNHU50orfwNUlZtV1GUqb77-2YDG-evpeX5_kObxSdUxhQgOTKfjg9SABSgCGwveiIgpQxCAn7feaMx1Sy98PoOIQPAJBC0KPI5-Sls966YBuru3plSb5ceod6TjpH6CWL87ZeOJI32s1dE8iTd11PWkMwkGKtm1qTAn2JLXY2XJOHemG7vluFAZnNrW-dWS-w3VBu0XnXnEYHFTbBnv3ek-j19mZWjOPJdHRX5JNYM0FZjMwIa7ikNKlkUpmSYsmFGGZlikmWUa0rZGVVGk4TBATDM5sybUQpSxSGsZPoYvt3jo1a-rpFv1YOazXOJ2rTAdB0KHm2oj072LLauxC8rXYCBbVZV23WVbt1e0Fuha-6set_aHVzPy3-uvHWrUNnv3cu-k8lUpYO1dvjSPHnCafjt7G6Zz_IVo4y</recordid><startdate>200709</startdate><enddate>200709</enddate><creator>Broustal, Garance</creator><creator>Ariza, Xavier</creator><creator>Campagne, Jean-Marc</creator><creator>Garcia, Jordi</creator><creator>Georges, Yohan</creator><creator>Marinetti, Angela</creator><creator>Robiette, Raphaël</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-4943-047X</orcidid><orcidid>https://orcid.org/0000-0002-4414-073X</orcidid></search><sort><creationdate>200709</creationdate><title>A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control</title><author>Broustal, Garance ; Ariza, Xavier ; Campagne, Jean-Marc ; Garcia, Jordi ; Georges, Yohan ; Marinetti, Angela ; Robiette, Raphaël</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3613-a3d6ed49112f92fdb1ab46658b7a2881ccfa3bfbd412a0a0d48e73cd6b9ba6d33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>1,5‐Diols</topic><topic>5-Diols</topic><topic>Aldol reactions</topic><topic>Allylation</topic><topic>Carbamates</topic><topic>Chemical Sciences</topic><topic>Organic chemistry</topic><topic>Palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Broustal, Garance</creatorcontrib><creatorcontrib>Ariza, Xavier</creatorcontrib><creatorcontrib>Campagne, Jean-Marc</creatorcontrib><creatorcontrib>Garcia, Jordi</creatorcontrib><creatorcontrib>Georges, Yohan</creatorcontrib><creatorcontrib>Marinetti, Angela</creatorcontrib><creatorcontrib>Robiette, Raphaël</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Broustal, Garance</au><au>Ariza, Xavier</au><au>Campagne, Jean-Marc</au><au>Garcia, Jordi</au><au>Georges, Yohan</au><au>Marinetti, Angela</au><au>Robiette, Raphaël</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2007-09</date><risdate>2007</risdate><volume>2007</volume><issue>26</issue><spage>4293</spage><epage>4297</epage><pages>4293-4297</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Direct enantiocontrolled access to 1,3‐amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama‐aldol addition). The obtained δ‐hydroxyesters were reduced to pent‐2‐ene‐1,5‐diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3‐asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six‐membered‐ring cyclic carbamates. Calculations enabled us to rationalize the observed stereoselectivity. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2007)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200700503</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-4943-047X</orcidid><orcidid>https://orcid.org/0000-0002-4414-073X</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European Journal of Organic Chemistry, 2007-09, Vol.2007 (26), p.4293-4297
issn 1434-193X
1099-0690
language eng
recordid cdi_hal_primary_oai_HAL_hal_00175948v1
source Wiley
subjects 1,5‐Diols
5-Diols
Aldol reactions
Allylation
Carbamates
Chemical Sciences
Organic chemistry
Palladium
title A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T22%3A05%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Stereoselective%20Approach%20to%201,3-Amino%20Alcohols%20Protected%20as%20Cyclic%20Carbamates:%20Kinetic%20vs.%20Thermodynamic%20Control&rft.jtitle=European%20Journal%20of%20Organic%20Chemistry&rft.au=Broustal,%20Garance&rft.date=2007-09&rft.volume=2007&rft.issue=26&rft.spage=4293&rft.epage=4297&rft.pages=4293-4297&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.200700503&rft_dat=%3Cwiley_hal_p%3EEJOC200700503%3C/wiley_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3613-a3d6ed49112f92fdb1ab46658b7a2881ccfa3bfbd412a0a0d48e73cd6b9ba6d33%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true